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Construction of Phosphole-Containing Hybrid pi-Conjugated Molecules and Their Application to Organic Devices

Research Project

Project/Area Number 25288020
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionNiigata University

Principal Investigator

Matano Yoshihiro  新潟大学, 自然科学系, 教授 (40231592)

Co-Investigator(Renkei-kenkyūsha) NAKANO Haruyuki  九州大学, 理学研究科, 教授 (90251363)
KIMURA Yoshifumi  同志社大学, 理工学部, 教授 (60221925)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥18,850,000 (Direct Cost: ¥14,500,000、Indirect Cost: ¥4,350,000)
Fiscal Year 2015: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2014: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2013: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
Keywordsホスホール / チオフェン / トリアリールアミン / 電荷移動特性 / 色素増感太陽電池 / 光電変換効率 / 蛍光発光特性 / D-π-A型色素 / 分子内電荷移動特性 / ホスホニウム塩 / 重原子効果 / 対アニオン / 溶媒効果 / クロスカップリング / 分子内電荷移動 / ボリル基 / 発光特性 / チタナサイクル / ターチオフェン
Outline of Final Research Achievements

New efficient methods for the synthesis of phosphole/thiophene-containing π-conjugated molecules were established, and their structure-property relationships were unveiled using various spectroscopic techniques and X-ray diffraction analyses. Some derivatives with high visible-light absorbing ability were used for organic solar cells. In addition, a new class of highly fluorescent derivatives was constructed. All the results show that the newly constructed phosphole/thiophene-containing hybrid derivatives would be promising candidates as organic materials.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (23 results)

All 2016 2015 2014 2013

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 3 results) Presentation (15 results) (of which Int'l Joint Research: 3 results,  Invited: 8 results) Book (1 results)

  • [Journal Article] Effects of Boryl, Phosphino, and Phosphonio Substituents on the Optical, Electrochemical, and Photophysical Properties of 2,5-Dithienylphospholes and 2-Phenyl-5-thienylphospholes2016

    • Author(s)
      Yoshinari Koyanagi, Yoshifumi Kimura, and Yoshihiro Matano
    • Journal Title

      Dalton Trans.

      Volume: 45 Issue: 5 Pages: 2190-2200

    • DOI

      10.1039/c5dt03362d

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Comparison of 2-Arylnaphtho[2,3-b]phospholes and 2-Arylbenzo[b]phospholes: Effects of 2-Aryl Groups and Fused Arene Moieties on Their Optical and Photophysical Properties2015

    • Author(s)
      Yoshihiro Matano, Yuta Motegi, Shinsuke Kawatsu, and Yoshifumi Kimura
    • Journal Title

      J. Org. Chem.

      Volume: 80 Issue: 11 Pages: 5944-5950

    • DOI

      10.1021/acs.joc.5b00541

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Structure-Property Relationships of Phosphole-Based π-Systems and Their Applications in Organic Solar Cells2015

    • Author(s)
      Yoshihiro Matano
    • Journal Title

      The Chemical Record

      Volume: 15 Issue: 3 Pages: 636-650

    • DOI

      10.1002/tcr.201402101

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] N,S,P-Hybrid Donor-pi-Acceptor Organic Dyes for Dye-Sensitized Solar Cell: Synthesis, Optical Properties, and Photovoltaic Performances2014

    • Author(s)
      Yoshihiro Matano, Yukiko Hayashi, Haruyuki Nakano, and Hiroshi Imahori
    • Journal Title

      Heteroatom Chem.

      Volume: 25 Issue: 6 Pages: 533-547

    • DOI

      10.1002/hc.21188

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Phosphole and Benzodithiophene-Based Copolymers: Synthesis and Application to Organic Photovoltaics2014

    • Author(s)
      Yoshihiro Matano, Hiroshi Ohkubo, Tetsushi Miyata, Yusuke Watanabe, Yuriko Hayashi, Tomokazu Umeyama, and Hiroshi Imahori
    • Journal Title

      Eur. J. Inorg. Chem.

      Volume: 2014 Issue: 10 Pages: 1620-1624

    • DOI

      10.1002/ejic.201301132

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 2-Alkenyl- and 2-Alkynyl-benzo[b]phospholes by Using Palladium-Catalyzed Cross Coupling Reactions2013

    • Author(s)
      Yoshihiro Matano, Yukiko Hayashi, Kayo Suda, Yoshifumi Kimura, Hiroshi Imahori
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 17 Pages: 4458-4461

    • DOI

      10.1021/ol401994e

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Charge-Carrier Transport Properties of Poly(phosphole P-alkanesulfonylimide)s2013

    • Author(s)
      Yoshihiro Matano, Hiroshi Ohkubo, Yoshihito Honsho, Arihiro Saito, Shu Seki, Hiroshi Imahori
    • Journal Title

      Org. Lett

      Volume: 15 Issue: 4 Pages: 932-935

    • DOI

      10.1021/ol4000982

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] Phosphole-based Organic Materials: Synthesis and Applications to Organic Solar Cells2015

    • Author(s)
      Yoshihiro Matano
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ホスホニオ基を有するπ共役ホスホールの合成と発光特性2015

    • Author(s)
      小柳誉也・木村佳文・俣野善博
    • Organizer
      第42回有機典型元素化学討論会
    • Place of Presentation
      名古屋大学野依記念学術交流館(愛知県名古屋市)
    • Year and Date
      2015-12-03
    • Related Report
      2015 Annual Research Report
  • [Presentation] 2-Arylnaphtho[2,3-b]phospholes and 2-Arylbenzo[b]phospholes: Synthesis, Structures, and Optical Properties2015

    • Author(s)
      Yoshihiro Matano, Yuta Motegi, Shinsuke Kawatsu, Yoshifumi Kimura
    • Organizer
      11th International Conference on Heteroatom Chemistry
    • Place of Presentation
      Caen (France)
    • Year and Date
      2015-06-14
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Optical Properties of Highly Fluorescent π-Conjugated Phosphole Derivatives2015

    • Author(s)
      Yoshihiro Matano
    • Organizer
      10th Organoelement Chemistry Seminar
    • Place of Presentation
      京都大学化学研究所(京都府宇治市)
    • Year and Date
      2015-06-08
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 2,5-ジチエニルホスホールの光物性に対する末端置換基の効果2015

    • Author(s)
      小柳誉也、木村佳文、俣野善博
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日大船橋キャンパス(船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] クロスカップリング反応を利用した2-アリールナフト[2,3-b]ホスホール誘導体の合成2015

    • Author(s)
      茂木祐太、俣野善博、木村佳文
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日大船橋キャンパス(船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] グリーンケミストリーを指向した典型元素有機化学2015

    • Author(s)
      俣野善博
    • Organizer
      グリーンケミストリー第5回研究シンポジウム
    • Place of Presentation
      新潟大学(新潟市)
    • Year and Date
      2015-03-17
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] クロスカップリング反応を利用した縮環ホスホール誘導体の化学修飾2014

    • Author(s)
      俣野善博、茂木祐太、河津信介、木村佳文
    • Organizer
      第41回有機元素化学討論会
    • Place of Presentation
      宇部市文化会館(宇部市)
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ジチエニルホスホールを母核とする新規π共役ホスホール誘導体の合成2014

    • Author(s)
      小柳誉也、木村佳文、俣野善博
    • Organizer
      第41回有機元素化学討論会
    • Place of Presentation
      宇部市文化会館(宇部市)
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis, Optical Properties, and Photovoltaic Performances of Phosphole- Containing Donor–π–Acceptor Organic Dyes2014

    • Author(s)
      Yoshihiro Matano, Yukiko Hayashi, Hiroshi Imahori
    • Organizer
      20th International Conference on Phosphorus Chemistry
    • Place of Presentation
      Dublin (Ireland)
    • Year and Date
      2014-06-27 – 2014-07-02
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ホスホールを含む新しい増感剤の開発と色素増感太陽電池への応用2014

    • Author(s)
      俣野善博
    • Organizer
      俣野善博第4回元素化学懇談会
    • Place of Presentation
      近畿大学(東大阪市)
    • Year and Date
      2014-06-21
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 15族元素の特徴を活かした反応剤と機能性材料の開発2013

    • Author(s)
      俣野善博
    • Organizer
      第48回有機反応若手の会
    • Place of Presentation
      守谷市
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] ホスホールを含む新奇なπ共役分子の創製2013

    • Author(s)
      俣野善博
    • Organizer
      統合物質創製化学推進事業第4回若手研究会
    • Place of Presentation
      名古屋市
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 高い可視光捕集能を持つ新規D-π-A型ホスホール誘導体の合成と色素増感太陽電池への応用2013

    • Author(s)
      林悠紀子、俣野善博、今堀 博
    • Organizer
      第40回有機典型元素化学討論会
    • Place of Presentation
      東大阪市
    • Related Report
      2013 Annual Research Report
  • [Presentation] 色素増感太陽電池への応用をめざした新規π共役ホスホールの合成2013

    • Author(s)
      林悠紀子、俣野善博、須田佳代、木村佳文、今堀 博
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      東京都
    • Related Report
      2013 Annual Research Report
  • [Book] Organic Redox Systems: Synthesis, Properties, and Applications2015

    • Author(s)
      Yoshihiro Matano
    • Publisher
      Wiley-VCH
    • Related Report
      2015 Annual Research Report

URL: 

Published: 2013-05-21   Modified: 2019-07-29  

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